(3R)-3,7-dimethyloctane-1,6,7-triol

Base Information

• Chemical Name: (3R)-3,7-dimethyloctane-1,6,7-triol
• CAS No.: 136180-09-1
• Molecular Formula: C₁₀H₂₂O₃
• Molecular Weight: 190.283
• Mol file: 136180-09-1.mol

Synonyms:

Chemical Property of (3R)-3,7-dimethyloctane-1,6,7-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R)-3,7-dimethyloctane-1,6,7-triol

There total 1 articles about (3R)-3,7-dimethyloctane-1,6,7-triol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(R)-5-((Ξ)-3,3-dimethyl-oxiranyl)-3-methyl-pentan-1-ol (1564-98-3,31560-68-6) → (3R)-3,7-dimethyloctane-1,6,7-triol (31558-25-5,136180-09-1)

Guidance literature:

With aluminum oxide;

DOI:10.1016/S0040-4020(01)90716-1

Reference yield:

(3R,6S)-2,3,8-trihydroxy-2,6-dimethyloctane (31558-25-5,136180-09-1) → C26H42O4

Guidance literature:

Multi-step reaction with 13 steps

1.1: toluene-4-sulfonic acid / dichloromethane / 0.17 h / 22 °C / Inert atmosphere

2.1: Dess-Martin periodane / dichloromethane / 0.25 h / 22 °C / Inert atmosphere

3.1: sodium chlorite; 2-methyl-but-2-ene; NaH₂PO₄ / water; tert-butyl alcohol / 0.17 h / 0 °C / Inert atmosphere

4.1: triethylamine / acetonitrile / 1 h / 0 °C / Inert atmosphere

5.1: tetrahydrofuran; acetonitrile / 1 h / 22 °C / Inert atmosphere

6.1: lithium chloride; diisopropylamine; n-butyllithium / hexane; tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

6.2: 2 h / 0 °C / Inert atmosphere

7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 22 °C / Inert atmosphere

7.2: 0.5 h / 22 °C / Inert atmosphere

8.1: 1H-imidazole / dichloromethane / 2 h / 22 °C / Inert atmosphere

9.1: diethyl ether / 6 h / -78 - 0 °C / Inert atmosphere

9.2: 0.5 h / 0 °C / Inert atmosphere

10.1: hydrazine hydrate / ethanol / 6 h / 70 °C / Inert atmosphere

11.1: iodine; triethylamine / tetrahydrofuran; dichloromethane / 0.5 h / 0 °C / Inert atmosphere

12.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium hydroxide / tetrahydrofuran; water / 2 h / 22 °C / Inert atmosphere

13.1: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 22 °C / Inert atmosphere

With 1H-imidazole; sodium chlorite; n-butyllithium; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; 2-methyl-but-2-ene; hydrazine hydrate; NaH₂PO₄; tetrabutyl ammonium fluoride; iodine; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; triethylamine; diisopropylamine; 9-bora-bicyclo[3.3.1]nonane; lithium chloride; sodium hydroxide; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; acetonitrile; tert-butyl alcohol; 2.1: |Dess-Martin Oxidation / 6.1: |Myers Asymmetric Alkylation / 12.1: |Suzuki-Miyaura Coupling;

DOI:10.1021/jacs.8b05070

Reference yield:

(3R,6S)-2,3,8-trihydroxy-2,6-dimethyloctane (31558-25-5,136180-09-1) → C38H54O7

Guidance literature:

Multi-step reaction with 10 steps

1.1: toluene-4-sulfonic acid / dichloromethane / 0.17 h / 22 °C / Inert atmosphere

2.1: ortho-nitrophenyl selenocyanate; tributylphosphine / tetrahydrofuran / 0.5 h / 22 °C / Inert atmosphere

2.2: 0.5 h / 0 °C / Inert atmosphere

2.3: 6 h / 40 °C / Inert atmosphere

3.1: ozone / dichloromethane; methanol / -78 °C

3.2: 1 h / -78 - 0 °C / Inert atmosphere

4.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 1 h / 0 - 22 °C / Inert atmosphere

5.1: sparteine; sec.-butyllithium / hexane; diethyl ether / 6 h / -78 °C / Inert atmosphere

5.2: 75 h / -78 °C / Inert atmosphere; Reflux

6.1: tert.-butyl lithium / hexane; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

6.2: 1 h / -78 °C / Inert atmosphere

6.3: 1 h / -78 - 0 °C / Inert atmosphere

7.1: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 22 °C / Inert atmosphere

8.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.25 h / 22 °C / Inert atmosphere

9.1: tri-n-butyl-tin hydride; triethyl borane / hexane; toluene / 0.5 h / 22 °C

10.1: Burgess Reagent / toluene / 1 h / 50 °C / Inert atmosphere

With ortho-nitrophenyl selenocyanate; Burgess Reagent; triethyl borane; tributylphosphine; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; tert.-butyl lithium; sec.-butyllithium; tri-n-butyl-tin hydride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; ozone; acetic acid; triphenylphosphine; sparteine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; toluene; 4.1: |Mitsunobu Displacement / 8.1: |Dess-Martin Oxidation / 9.1: |Reformatsky Reaction;

DOI:10.1021/jacs.8b05070

upstream raw materials:

(R)-5-((Ξ)-3,3-dimethyl-oxiranyl)-3-methyl-pentan-1-ol

Downstream raw materials:

Toluene-4-sulfonic acid (3R,6S)-6,7-dihydroxy-3,7-dimethyl-octyl ester